


Win/Win

by jessicarocket



Category: Pocket Monsters | Pokemon (Anime)
Genre: F/M, Friends to Lovers, Mild Smut, RocketShipping - Freeform, Team Rocket (Pokemon), Unresolved Sexual Tension
Language: English
Status: Completed
Published: 2020-01-08
Updated: 2020-01-08
Packaged: 2021-02-27 10:42:20
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,438
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22175755
Author URL: https://archiveofourown.org/users/jessicarocket/pseuds/jessicarocket
Summary: Jessie and James get into a heated battle over a sweet treat. Who will be the winner?
Relationships: Kojirou | James & Musashi | Jessie, Kojirou | James/Musashi | Jessie
Comments: 9
Kudos: 84





	Win/Win

**Author's Note:**

> Hi guys!!! It's been a while! I started this fic back in September 2018, back when I was still in a nice, consistent writing groove. About halfway through this, I full into a rut and I've been on a bit of a hiatus from writing since then. A surge of motivation/inspiration hit me this week so I decided to go ahead and finish and share this fic. I'm pretty rusty on writing fiction, but hopefully you guys will find some enjoyment in this anyway!
> 
> Thank you for reading! Please let me know what you think in the comments. Reviews fuel me!

A comfortable sense of quiet hung over the base as morning began to stretch into afternoon. With the exception of raindrops gently pattering against the roof, the room was soothingly absent of the usual cloud of chaos the team seemed to carry wherever they roamed. With the downpour continuing steadily for hours with no end in sight, the group had collectively chosen to take the day off rather than waste it inside the malasada truck. The likelihood of hungry customers roaming the streets on foot in such dreary weather was about as high as the trio retaining that coveted pikachu long enough to deliver him to the boss, though this was a fact none would ever admit aloud.

Jessie lazily flipped the pages of a months-old issue of Pokepolitan, eyes idly scanning over the words and images but finding little that captivated her interest. She shifted her weight back in the chair as she slung her feet onto the small kitchen table, crossing her legs at the ankles with a listless sigh. James was seated directly across from her, slouched over the table with hands busy as he feverishly polished every millimeter of his prized his pokeball collection. The skin between his eyebrows creased as he carefully scanned the sleek metal surfaces for any tiny imperfections that needed to be buffed out. Meowth was perched on the table just inches away, resting on his side with his head propped on one paw. He emitted periodic yawns as his consciousness drifted between the waking and sleeping worlds.

Jessie dipped her weathered manicure into a bowl on the center of the table, searching for a prize by touch without taking her eyes off the magazine page. As her fingers drifted to the bottom of the bowl and grasped the last remaining honey malasada, she found them colliding with another set of fingers that belonged to her human companion. Both pairs of eyes locked on one another, abandoning their previous tasks as they came to the realization that there was only one malasada remaining for two eager mouths. Any sense of peace that had filled their living quarters previously was long gone, replaced by a palpable tension.

Jessie was the first to break the thick silence in a calm, matter-of-fact tone that was betrayed only by the intensity of her piercing gaze.

“I reached for it first.”

James’ voice followed in a much less controlled manner, his pitch increasing into a whine with each word. “You did not! We both touched it at the exact same time!”

Jessie’s bellow of “ _Not true!_ ” shook the walls of the base.

The shift in atmosphere and sudden burst of words jolted Meowth awake as he sat up and turned toward the sources. _Here we go again_ , he thought with a roll of his eyes.

James took a calming breath. “Look, there’s no need for us to argue over something so trivial. Let’s just share it!” Noticing Meowth’s movement from the corner of his eye, James turned toward his feline partner. “Do you want a piece, too, Meowth? We can easily split it three ways.”

With a chuckle, Meowth shook his head. “Nah. T’anks for t’inkin’ of me, Jimmy. But I’m good.” Another malasada had materialized in his paw, much to the dismay of both humans.

“How...”

“Where…”

“ _You don’t even have pockets?!_ ” they shouted in unison.

A mischievous grin spread across his face briefly before he opened his jaw with an unrefined _smack_ and consumed the entire pastry in a single bite. With a loud cackle, and he hopped off the table, briefly landing on all fours before resuming the human-esque stance that distinguished him from your run-of-the-mill street meowth. He turned his back on both partners and strolled toward the bedrooms, casually calling “Play nice, youse two!” over his shoulder with a casual wave of his paw.

The eyes of both humans remained fixed on Meowth until he vanished from their line of sight. With a slam of a door echoing across the base, Jessie and James returned their gazes to each other, not realizing until that moment that neither had released the honey malasada in the midst of their teammate’s dramatic show.

James felt his breath hitch under his partner’s stare as his mind become entranced by each line and curve of her flawless face. His mind slowly sank into a sea of dangerously romantic thoughts about his partner as he wondered how it was humanly possible for anyone to look so _exquisite._ Her knuckles lightly brushed against his as she attempted to get a firmer grip on the sugary treat between them. This unexpected physical contact, as small and simple as it was, sent his heart racing.

Attempting to regain control of his functions, James returned his attention to the malasada. “Seriously, Jess. Let’s just split it! It’s quite sizeable, so there is plenty for both of us to be satisfied.” He grinned at her, lowering his voice and forcing the smoothest tone he could muster despite the flutter that still refused to leave his heart. “It’s a win-win.”

“No.” Jessie’s reply was curt and threw James completely off kilter.

James could only manage to echo her, his voice ripe with confusion as he tried to decipher the intentions behind it.

“No. We split things back when we were starving. We’re not that poor anymore.”

“Touche…” James’ gaze shifted between Jessie’s frustratingly flawless face and the malasada, which was still in the firm grips of their opposing hands. His eyes scanned scanned her expression, hoping for a sign of where this was leading but coming up empty. The suspense left him breathless, wondering if she would ever clarify her intentions or instead leave him staring at her for the rest of eternity. For a moment, he began to wonder if he could ever look away from her again. Her face was a work of art that he hoped to forever burn into his brain, in hopes that it would be the one image left when everything else faded over time.

James was awoken from his daydream with a jolt as Jessie finally ended the silence that had stretched between them.

“We’re going to fight for it.” Her facial expression remained neutral and her tone flat, creating an almost comedic effect in the way they clashed with the weight of her words. The longer James studied her face, more the dissonance tickled him until a giggle forced its way up his throat and past his lips.

Her eyes narrowed, silencing him instantly. “I’m being serious, James. We’re going to fight for it. The winner takes it all.”

The absurdity of the situation left James all the more humored, but he swallowed his remaining laughter as his fingers finally released the malasada. “It’s all yours, dearest. The last thing I want to do is fight you over food when, like you said, we’re no longer experiencing that particular brand of poverty.” He pushed the bowl toward her, waving his metaphorical white flag in surrender.

Two tightly clenched fists slammed against the table, resulting in a short but abrupt sound that seemed to rattle every wall of the base. In the silence that followed, the faint but unmistakable sound of Meowth yelping a string of expletives from the bedroom could be heard, followed by unintelligible chatter from the other pokemon.

“Come _on_ , James. You’re just going to roll over and give up before you’ve even tried? What kind of Team Rocket agent are you? Where’s your fighting spirit?!”

Jessie’s fists remained clenched as they pressed against the unyielding surface of the table top, weathered nails digging into her palms. Her eyes narrowed as she stared James down, unblinking. 

James couldn’t help the smile that tugged at the corners of his mouth as he noted how powerless he was against her passion.

“Ok, Jess. Fine. How exactly do you propose we go about this, erm... fight?”

Her expression softened into one that was more pensive. “I hadn’t thought that far.”

James fought the urge to laugh, having enough sense to know it wouldn’t be well-received in this sort of situation. “How about something like… I don’t know? Rock, Paper, Scissors?”

Jessie paused for a moment, her expression becoming unreadable yet again. With a shrug and a roll of her eyes, she replied, “Well, that’s a little bit _mild_ for my taste, but sure. We can start there.”

Following a countdown, two clenched fists were thrust simultaneously into the space between their bodies. Rock versus rock. A tie. Without missing a beat, they launched into another round, resulting in two flattened hands, palms facing down. Paper versus paper. Another tie.

This sequence repeated again and again, resulting in both presenting the same gesture each time as their voices became louder and their movements more animated with each round. The synchronicity continued despite their best efforts of break it, eventually coming to a half as both simultaneously thrust a finger in the other’s face with a shrill “ _Stop copying me!!!_ ”

They remained frozen, panting and exchanging glares as their minds searched for a logical explanation for the fact that they had somehow become so in sync even in situations that didn’t involve well-rehearsed motto. Though neither dared to vocalize it, they both felt an unusual pull between them, like two magnets being drawn together by an invisible but overwhelmingly powerful force.

In an effort to squelch the sensation, Jessie forced her attention back to the source of their problem. With a frantic dart of her arm, she snatched the lonesome malasada from the depths of the bowl and turned to flee. Before she could get a safe distance from her partner, she felt both of his arms wind around her waist from behind, grasping blindly for the pastry. Her arms shot into the air as high as she could muster without fully considering the fact that this would not adequately remove the item from her partner’s reach. In an instant, he gripped her waist and twirled her around to face him.

“That’s not fair, Jessie! It was a tie! Why are you snatching the prize and acting like _you_ were the victor?!”

“Because I _am!_ ”

To punctuate her final word, she pressed her free palm against James’ chest and shoved him roughly. His hands had retained a tight grip on her waist, and instead of the shove having the desired effect of removing him from her proximity, it effectively sent him off-balance as he pulled her down with him. James was unable to properly brace himself for the fall as he landed flat on his back against the unforgiving floor, the impact magnified by the addition of Jessie’s body landing on top his. A heap of limbs tangled together as their torsos pressed against one another. The impact of the fall had knocked the wind out of both, leaving them temporarily stunned and immobilized.

“ _Now_ I win.” Jessie’s head rested at an angle which allowed her breathy words to softly tickle James’ ear with each syllable, the unmistakable feeling of her breasts pressing against his own chest. He shuddered beneath her, an involuntary moan escaping him before he had an opportunity to regain his wits.

The sound he emitted, strained yet almost primal in nature, fully ignited the spark Jessie had been trying her damndest to extinguish. As she pressed herself into a sitting position, she found her legs wrapped around his as she straddled his lap. Meanwhile, the added pressure against James’ groin paired with the sight of the hem of Jessie’s skit gliding up the porcelain skin of her thigh left James feeling as though the wind had been knocked out of him again. After another beat, his brain sluggishly caught up to his body, eyes widening as he realized the compromising position they had landed.

His panic only escalated as he felt a telltale twitch in his groin. If he didn’t get Jessie off of him rather quickly, she would soon feel a very obvious physical manifestation of the uncontrollable desire that was coursing through his veins as he gazed at her.

Gripping her arms, he focused every ounce of his strength in lifting her body from his. After several unsuccessful attempts to gain some form of leverage between the unyielding firmness of the floor and that of Jessie’s body, he put all the strength he could muster into an attempt at rolling out from underneath her. Despite every method of escape he tried, he still found himself hopelessly trapped between her thighs. That curvy set of thighs that consumed him even when he closed his eyes in an attempt to shut them out.

He cursed himself for somehow forgetting how strong his partner was as images of her lifting and slinging his body around with ease danced across his consciousness. He cursed himself again for recalling memories that only seemed to fuel his arousal even further. With every movement he made in hopes of creating distance between their groins, he only created more delicious friction as their bodies grinded together.

“Jessie! Please get off me! _Please!_ ” He cringed at the sound of his own pleading voice, a desperate air of urgency he so wished to mask.

Jessie gazed downward with a smirk that bordered somewhere between devilish and mocking. “What? Am I too heavy for the delicate rich boy?” She shifted her weight in a way that pinned him against the floor with greater force. “You know, it’s awfully rude to insinuate such a thing about me.”

James’ hands had come to grip her hips with a ferocity she hadn’t felt from him before. The way his face scrunched as he continued to spew a series of pleading whines, a stark contrast to the suave demeanor he typically tried to portray, almost struck her as comical. As her partner became increasingly unhinged beneath her, she found herself hurtling toward a fit of laughter until a very specific sensation between her legs stole her attention. Every nerve in her body had become acutely aware of a growing bulge in her partner’s pants. This unexpected feeling of his hardness pressed against her sent shivers down her spine and a gasp escaped her lips before she could even consider containing it.

It didn’t take James long to read her sudden stillness and realize that, despite his best efforts, his body had betrayed him and sent his best friend a very overt sign of his affections toward her. His horror only multiplied as he desperately searched for words and came up empty. As much as he longed to be the smooth talker who could blend the perfect set of words to cure any ailment, all of his flowery prose were locked behind the thick walls of a vault inside his mind anytime panic set in. James’ mouth began to flap wordlessly, reminding Jessie briefly of a magikarp. Her mouth curled into a grin.

“Oh, my. Is that what I think it is?” She pressed herself even more firmly against his budding erection for emphasis. 

His voice returned, tumbling out of him in a heap of desperate apologies. “J-Jessie! I’m sorry! I’m so sor-”

She silenced him with single finger pressed against his lips and leaned forward until her face was inches above his. Noting the hunger in James’ eyes and the way his breathing had become increasingly ragged, Jessie felt drunk on her own power and lust. She suddenly wanted nothing more than to take this game as far as it could go. With a thick cloud of feelings swirling inside her chest, she silently wondered if any of this could even be considered a game anymore. Perhaps the spark between them had always been more real than she had ever wanted to admit to herself.

“Well, aren’t you a dirty boy.” Her words were punctuated with a tone more sultry than James had ever imagined in his wildest, wettest dreams. A powerless squeak was all he could muster in reply as his fingers dug further into the fabric across her hips.

She shifted her lips toward his ear, whispering another “dirty boy” as she grinded against him ever so slightly. James was deliciously responsive, his pelvis jutting against hers as a low groan escaped his throat.

They had officially crossed an invisible border, one that they had danced along many times, and entered uncharted territory together. There was no turning back now. 

Jessie pressed her lips against James’ fervently, pleased to find him greeting her kiss with equal enthusiasm. Lips parted, tongues tangled, and fingers intertwined in hair in a feverish attempt to close every millimeter of space between them. They were overcome with an urge to melt into one another. To become so tangled with the other that they could never be separated again. The world around them seemed to fade into a cloudy haze, their senses tuned into nothing but the feel and smell of each other's skin and sound of each other's breaths. All sense of time and place was lost between them. Nothing else existed or mattered.

James’ hands shifted from Jessie’s hips to her bare thighs, slowly gliding upward until they found the hem of her skirt. He paused briefly to gauge her reaction and was rewarded with an urgent moan from her mouth into his. His hands slid underneath her skirt, his fingertips softly stroking the hem of her panties.

With that, the last remaining thread of Jessie’s strength snapped, and she tore her partner’s shirt and jacket off in one rough motion before doing the same to her own. The needy whines James emitted each time their lips parted momentarily only fueled Jessie’s fire even further. He was starving for her, and her for him.

Jessie roughly gripped at James’ belt, clumsily yanking to unbuckle it and cast it aside, desperate for the final barriers between them to disappear more quickly.

With Jessie’s hands on the waist of James’ unfastened pants and his on the hem of her skirt, they found themselves in a tangle of limbs as both fought to remove the other's clothing as if their lives depended on it.

And then everything came to a screeching halt. They paused, staring at one another breathlessly.

Jessie was the first to speak, her senses clouded by the feel of James' hands on her skin and the scent of his rose shampoo swirling around her. “Did… did you hear something?”

A familiar voice answered before James had a chance to catch up. “Yeah, you did hear somet’in’. It was me calling youse two nasty fucks. Because dat's what ya are. Nasty fucks.”

Both humans slowly peeled their gazes from one another and followed the direction of the voice. There stood their feline partner, arms crossed with his face twisted in a scowl. 

With a shake of his head, Meowth scolded them. “Did you numskulls really t’ink dis was a good idea? James, whaddya t’ink would happen if Mareanie was da one who busted in on dis instead o’ me? Or what if da boss called while youse two was busy doin' da horizontal tango?"

Both humans shuddered at the thought. Lying half naked in a heap on the floor, sweat still glistening on their skin, the gravity of them nearly having had sex in the main room of their base with their entire pokemon family in the next room finally began to sink in.

Meowth clicked his tongue and shot them another disapproving look. “Guess I need t’ do a bettah job babysittin’ you bozos. Better get dressed quick ‘cause I don’t know how long I can distract da other two.”

With that, Jessie and James hopped to their feet and briskly sorted through the heap of uniform bits scattered across the floor around them. As James ran his palm against the fabric of his pants in an effort to smooth out a line of wrinkles, he felt a pair of arms wind around his waist. Before he could react, Jessie’s hot breath danced against his neck and her whispers caressed his ear, eliciting a shiver down his spine.

“We’ll finish this later. We still need to find out who wins the tie-breaker.”

With a coy wink over her shoulder, she made her way back onto her chair and resumed her task of listlessly flipping through magazine pages.

James slumped back into his own chair and ran his hand through tangled strands of lavender. His became face consumed by a dreamy grin, no longer caring about the outcome of the malasada as he considered the possibility that this "tie-breaker" could end up being a win/win for them both.


End file.
